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I'm a 27 year old boomer. I owned physical cartridges of Blue and Gold for Gameboy color and those were my first ever pokemon games. I stopped playing pokemon with Gen 4, and only returned to Gen 5 and onwards as an adult, so I have no nostalgia for the later games.
Gen 5 is without a doubt the most innovative and challenging pokemon games ever made. You can tell a lot of passion was and a desire to make changes to the formula that had become stale were a big part of the game's design ethos, as well as trying to make games for an older audience. It treated pokemon fans with respect yet also refused to pander to them. It's also a straight up beautiful game with a gorgeous overworld that changes with the season and absolutely fantastic, handcrafted battle sprites.
It's a shame GameFreak overestimated the pokemon fanbase and the games did not sell well, as it taught them to never put any passion into making pokemon games instead and just to keep making the same games its fanbase always wanted.
The pokemon designs in gen 5 were lackluster though.